Over the next five years he directed his friends in forty-five short videos, by which time he realized that good storytelling was the key to good filmmaking. He was accepted to medical school but instead chose to attend the Tisch School of Arts at New York University to study filmmaking, all the while pursuing scriptwriting as well.

He finished his three-year program with seven new scripts of his own, and three months later began shooting one of them in Madras. This film was Praying With Anger, a film about an American-born Indian studying abroad in India which Night wrote, directed and produced, as well as acted in. In 1993 the American Film Institute bestowed upon him their Debut Film of the Year award for it. It was entirely on the recognition of this award that Night received an agent in Hollywood without having to leave Philadelphia.

Praying With Anger was followed in 1998 by Wide Awake, a family comedy which bombed at the box office. But Night had also been working on a script for E.B. White's classic book Stuart Little as well as his own story, The Sixth Sense.The Sixth Sense took him a year to write and was picked up quickly by Disney for $3 million. He received a $5 million paycheck for his next script, Unbreakable, which he directed for another $5 million (as well as acted a bit part in as an anonymous drug dealer), making him the highest paid scriptwriter in Hollywood today. Both The Sixth Sense and Unbreakable were based and filmed in Night's native Philadelphia; he refuses to move to California.

Night says he prefers the "immediate results" of directing to the laborious task of writing, but believes he cannot grow in his career without accomplishing both. Most fans would no doubt agree; Night is already establishing a signature style for his stories, including unexpected twist endings, that is nearly unique amid the big-budget and fairly predictable Hollywood blockbuster machines.